Every Thursday afternoon, I experience the same Groundhog Day conversation with the girls in my fashion department. They start to debate their weekend date wardrobes and, inevitably, this yammer yields a familiar dialogue:

Then my aha moment: I have come to realize that all women basically have two wardrobes—one to wear for other women (and themselves!) and one to wear for men. What works at brunch with girlfriends might not yield you that second date. It's a simple fact: He's Just Not That Into Your Skirt.

To the women in my office, I am this wise old fashion sage, constantly offering advice on what to wear and how to wear it. But when it comes to knowing what a real guy wants, how should I know? Sure, I'm a guy, but—and this is their theory—I'm a Fashion Guy. I'm the guy who goes shopping with you, not the guy who thinks Proenza Schouler is a retirement plan. A male friend—okay, he's a total dude—told me recently that men love contradiction. They want a woman in heels, but not high-maintenance; hot, but still presentable to Mom; able to swig a beer at a baseball game, but turning heads while doing it.

Okay, point taken. But does this really mean that my POV is insignificant when compared to that of the guy next door?

So I decided to solicit the help of a guy next door—actually, three blocks away at 30 Rock—Saturday Night Live's Andy Samberg. Andy is the perfect foil for me: laid-back, effortlessly hip, a hit with the ladies, and knows exactly what he likes, style-wise (including telling his publicist many times that her shoes were "bitchin' ").

And it was on: the Fashion Guy vs. the Funny, Cool Guy. I know my Dolce. He's got "Dick in a Box." I speak Lanvin. He raps "Lazy Sunday."

I invited Andy, who is one of the voices behind this month's animated film Cloudy With a Chance of Meatballs, to spend the day with me, style-plotting his way through various looks. We dressed some of the ELLE editors for certain situations where a dude's opinion matters to see how our styling contrasted. When I initially told the girls that we were both going to come up with looks that are chic and relevant to different dating scenarios, they chuckled (at me) and swooned (over him). But judge for yourself. Personally, I admit Andy did great. And I wasn't so bad either.

ROUND 1: EVENING OUT
Joe Zee vs. Andy SambergJOE WEIGHS IN: I love a lady to look like a lady. I love when not a hair is out of place...the perfect accessories...and oh, the dress—part '80s, part Christmas tinsel—it's pure chic sophistication. Shapeless never looked so good. (The secret is the belt.)ANDY WEIGHS IN: This is the evening gown version of when the Predator monster becomes reflecty and invisible. Soooooo, not a plus? I don't even know. I do like that movie.

Which look do you prefer?(polling)ROUND 2: HITTING THE CLUBS
Joe Zee vs. Andy SambergJOE WEIGHS IN: If you're going out, why not really go out? This is the perfect time to throw it all on—marabou bolero, crystal mini, glitter platform boots—because after three drinks, you'll look fabulous to everyone. They just won't remember in the morning.ANDY WEIGHS IN: I like this well enough. Jeans and high heels are always enjoyable, right? I'm drawing on my vast knowledge of clubbing at clubs here. Me and my friends will just club it up all night. Clubbin' around with our fellow clubbers!

Which look do you prefer?(opinion)ROUND 3: MEETING THE PARENTS
Joe Zee vs. Andy SambergJOE WEIGHS IN: Okay, you're going to meet his parents, not interview for prison admission (well, maybe). Still, where in the guidebook does it say that in-laws prefer drab and puritanical over style? I love a chic dress, but if you must, put a mom cardigan over it to say, "Hey, I can be just like you!"ANDY WEIGHS IN: Always err on the side of "nice" with the parents. I mean, you don't want them to think you're a dud, but no one ever came back from that experience like, "I shoulda went sluttier." (Note: This does not apply for dudes. If there's one thing I've learned, it's that dads love a boyfriend in a midriff tee.)

Which look do you prefer?(poll)ROUND 4: DRESSING FOR SUCCESS
Joe Zee vs. Andy SambergJOE WEIGHS IN: Give me lady-boss any day of the week. Loving the authoritative, in-command look here with the strict tailoring and classic, hard-to-walk-in pencil skirt. The major shoulder pads don't hurt either. So what if she looks like she'll kick your ass? Chic!ANDY WEIGHS IN: These are two great examples of office attire. On the one hand, there's the stylish and sexy look. Curvy, but authoritative, with just enough skin showing to really pique our interest. And then there's the outfit the girl's wearing. Punch line!!!

Which look do you prefer?(survey)ROUND 5: CHILLING ON THE WEEKEND
Joe Zee vs. Andy SambergJOE WEIGHS IN: I love a girl who doesn't care, but really does; effort without trying. Witness the carefully placed details: the nonchalant scarf, the laceless two-toned Top-Sider, and that extra-large L.L. Bean tote—obviously carrying her Birkin bag. Clearly she just left from the office.ANDY WEIGHS IN: I feel like most girls I know wear some form of this outfit. To me this look says, "Hey, I don't suck ass," which is an important place to start with people in general.

Which look do you prefer?(polls)ROUND 6: HAVING A FIRST DATE
Joe Zee vs. Andy SambergJOE WEIGHS IN: Being sexy doesn't mean showing it all off. I love this dress; covered up just enough and revealing just enough. You want to be ready to broker the deal—not show the deal is done!ANDY WEIGHS IN: Growing up in the '80s has left me basically helpless against this shade of pink. I also still like a leg warmer. But just one. Like an eye patch for your ankle.

Which look do you prefer?(surveys)ROUND 7: SKIPPING TOWN TOGETHER
Joe Zee vs. Andy SambergJOE WEIGHS IN: Not working doesn't mean you can't work it. This is how you do it: Start with a swimsuit—what guy doesn't love that?—and then layer ripped jeans, tops, jackets, and miniature dogs with it. Sunglasses optional.ANDY WEIGHS IN: Have you ever met a girl in this outfit who was a dick? The second best thing the Ramones gave us was the street hustler look for ladies.